Lefetamine
Title: Lefetamine
CAS Registry Number: 7262-75-1
CAS Name: (aR)-N,N-Dimethyl-a-phenylbenzeneethanamine
Additional Names: (-)-N,N-dimethyl-1,2-diphenylethylamine; (-)-N,N-dimethyl-a-phenylphenethylamine
Molecular Formula: C16H19N
Molecular Weight: 225.33
Percent Composition: C 85.28%, H 8.50%, N 6.22%
Literature References: Centrally acting analgesic with stereochemical resemblance to morphine, q.v. Prepn and activity: K. Ogiu et al., J. Pharm. Soc. Jpn. 80, 283 (1960); eidem, JP 61 23087 (1961 to Res. Found. Practical Life). Absolute configuration: M. Nakazaki, Chem. Ind. (London) 1962, 1577. NMR data indicates 22% eclipsed conformation which appears to enhance stereoselectivity for morphine receptors: T. Sasaki et al., J. Med. Chem. 9, 847 (1966). Pharmacology: H. Nakamura, M. Shimizu, Arch. Int. Pharmacodyn. Ther. 221, 105 (1976). Clinical study: J. P. Famaey, T. L. Peeters, Brux. Med. 56, 21 (1976). Analgesic activity: M. Nozaki et al., Life Sci. 33, Suppl. 1, 431 (1983). Opiate agonist activity: M. Graziella de Montis et al., Pharmacol. Res. Commun. 17, 471 (1985).
Properties: bp6 142-147°. [a]D20 -124.2° (ethanol).
Boiling point: bp6 142-147°
Optical Rotation: [a]D20 -124.2° (ethanol)
 
Derivative Type: Hydrochloride
CAS Registry Number: 14148-99-3
Trademarks: Santenol (Coop. Farm.); SPA (Santen)
Molecular Formula: C16H19N.HCl
Molecular Weight: 261.79
Percent Composition: C 73.41%, H 7.70%, N 5.35%, Cl 13.54%
Properties: mp 218-219°. [a]D20 -91.7° (water).
Melting point: mp 218-219°
Optical Rotation: [a]D20 -91.7° (water)
 
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.14.
Therap-Cat: Analgesic.
Keywords: Analgesic (Non-Narcotic).

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